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General procedure: A mixture of compound 3a (33.5 g, 0.15 mol), 4% NaOH solution (335 mL) and ethanol (335 mL) was heated to reflux for 3 h. Upon cooling to room temperature, the mixture was poured into ice-water, adjusted to pH 5 with glacial acetic acid, and then the precipitate was collected by filtration. 4a was obtained as a white solid (26.4 g, 90%).
6-Fluoro-1H-indole-2-carboxylic acid 12a (2.00g, 11.16mmol) was dissolved in 60mL of absolute ethanol, 10mL of 98% concentrated sulfuric acid was added, the reaction liquid was heated to 105C and was reacted for 2 hours. The pH of the reaction solution was adjusted to 7 to 8 with 1M NaOH, the solution was extracted with ethyl acetate (150mL*3). The combined organic phases were washed with saturated sodium chloride solution (2000mL*3) then saturated ammonium chloride solution (200mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain ethyl 6-fluoro-1H-indole-2-carboxylate 12b (2.24g, dark yellow solid), yield: 94.1 %. MS m / z (ESI): 207.9 [M + 1]
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